Nestled just a short 5-minute walk from the historic Village at Winona, Wanderer’s Rest is the ultimate premium home base for our region’s most popular annual festivals, winter recreation, markets, and events. Whether you are traveling with a large group of up to 21 in our full 7BR/5BA home, up to 14 in our 5BR/3BA main levels, or a smaller crew of up to 7 in our private 2BR/2BA Garden Suite, our flexible layouts put you right next to the action.

Planning a visit? Below are the premier annual events that bring our vibrant community and the surrounding lakes to life. Because exact weekend schedules can shift year to year, we’ve provided direct links to the official event organizers so you can verify current dates, view schedules, and register.

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Major Grace College Campus Events

As a proud neighbor of the Grace College campus, our property provides the ideal upscale retreat for visiting families, alumni, and athletic supporters. Skip the corporate hotels and enjoy being within a 5-minute walk of all major campus milestones.

Grace College Freshman Move-In Weekend (Mid-August)

• The Vibe: An exciting, milestone weekend as the campus welcomes incoming freshmen and their families to begin the academic year.
• The Highlights: Move-in day is filled with campus orientation events, parent informational sessions, and traditional welcome celebrations designed to help new students transition seamlessly into college life.
• The Wanderer’s Rest Advantage: Avoid the emotional rush of standard hotel rooms. Our spacious home offers a peaceful, private environment where families can enjoy their final home-cooked meals together, unpack gear comfortably, and enjoy a relaxed, meaningful send-off just a short walk from the dormitories.
• Official Details: View Grace College Orientation & Move-In Schedules

Grace College Family & Sibs Weekend (September)

• The Vibe: A special early-autumn campus tradition dedicated to bringing parents, siblings, and extended families together on campus to visit their students.
• The Highlights: The weekend features fun interactive events, sibling-focused activities, campus-wide community meals, and opportunities to experience student life firsthand alongside your student.
• Official Details: View Family & Sibs Weekend Details

Grace College Homecoming Weekend (Early October)

• The Vibe: A vibrant, celebratory weekend that brings together alumni, current students, and the local community to honor the college's heritage and reconnect.
• The Highlights: The campus comes alive with festive tailgates, alumni athletic matches, specialized theater performances, campus tours, and classic milestone class reunions.
• Official Details: View Grace College Homecoming Information

Grace College Commencement / Graduation Ceremonies (Early May)

• The Vibe: A milestone weekend celebrating the academic achievements of the graduating undergraduate and graduate classes.
• The Highlights: Centered around the main commencement ceremony, the weekend brings thousands of extended family members and friends to Winona Lake to celebrate their graduates.
• The Wanderer’s Rest Advantage: The perfect space for graduation hospitality! Our generous common spaces, full kitchens, and private layouts allow your entire extended family to cook celebratory meals, stay together under one roof, and walk to the ceremony without worrying about campus parking.
• Official Details: View Graduation Schedules & Details

NCCAA National Tournaments & Lancers Athletics (Year-Round / Varied)

• The Vibe: Elite collegiate sports competition as Grace College frequently serves as the host destination for major National Christian College Athletic Association national championship tournaments.
• The Highlights: From high-stakes national basketball and soccer tournaments to competitive track and field meets, the campus welcomes elite athletes and their fan bases from across the country.
• The Wanderer’s Rest Advantage: An exceptional fit for traveling athletic groups, coaching staffs, or large families of competitors who require dedicated workspace, full laundry facilities to manage gear, and quiet, high-end bedding to rest up before the big game.
• Official Details: View Grace College Athletics Schedules

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Seasonal Community Festivals & Events

Winter Ice Skating & "Stick & Puck" at the Miller Sunset Pavilion (November – March)

• The Vibe: Magical winter recreation hosted at the state-of-the-art, covered outdoor pavilion located right on the land where the historic Billy Sunday Tabernacle once stood.
• The Highlights: Enjoy public ice skating (complete with skate rentals, a cozy brick fireplace, and concessions) under the beautiful clerestory lights. For hockey enthusiasts, specialized "Stick & Puck" sessions are hosted weekly for players of all skill levels to practice stickhandling, passing, and light scrimmaging in a relaxed environment.
• Official Rink & Concession Hours: View Miller Sunset Pavilion Skate & Hockey Schedules

Pajama Party Sale (Late January)

• The Vibe: A highly anticipated winter shopping tradition that turns the cold season into a festive, community-wide celebration.
• The Highlights: Set your alarm! Starting at 7:00 AM, local Village shops offer their deepest discounts of the year—but there is a catch: you must be wearing your pajamas to get the deals!
• The Wanderer’s Rest Advantage: Don't worry about freezing cars or morning traffic. Roll out of bed at 6:45 AM, keep your pajamas on, and stroll right down the street into the shops. You can easily pop back to the house to drop off your shopping bags and warm up!
• Official Details: View Pajama Party Sale Details

Wine about the Winter (Early February)

• The Vibe: A cozy, warm-up winter stroll designed to celebrate great wine, local shopping, and the beauty of the snowy lakeside Village.
• The Highlights: Purchase a ticket to taste a variety of wonderful wines poured at cozy boutiques and artisan shops throughout the Village. It is the ultimate antidote to the winter blues and a spectacular excuse for a weekend trip.
• The Wanderer’s Rest Advantage: Perfect for a couples' trip or an adult friend group getaway. Walk to and from the wine tasting safely without needing a designated driver. Plus, our beautifully updated historic kitchen is the perfect spot to open an extra bottle and keep the evening going.
• Official Details: View Wine about the Winter Details

Village Madness (March)

• The Vibe: A month-long spring shopping event celebrating local business and small-town charm.
• The Highlights: Collect stamps as you shop and dine throughout the Village for a chance to win amazing gift baskets filled with local treasures.
• Official Details: View Village Madness Details

Girlfriends’ Weekend (Late April)

• The Vibe: The ultimate weekend escape to shop, dine, and unwind with your favorite people.
• The Highlights: Specialized trunk shows, exclusive boutique sales, free refreshments, and gift giveaways at shops throughout the Village.
• The Wanderer's Rest Advantage: Skip the cramped hotel rooms! Our home offers plenty of private beds, 5 full bathrooms, and gorgeous common spaces for late-night chats.
• Official Details: View Girlfriends’ Weekend Details

The Farmers Market at Winona (Saturdays, May – October)

• The Vibe: A bustling community gathering place featuring the freshest local produce, meats, baked goods, plants, and artisan foods.
• The Highlights: Hosted under the gorgeous, covered Miller Sunset Pavilion (rain or shine) from 8:00 AM to 1:00 PM. Enjoy ready-to-eat foods and local food trucks with plenty of outdoor seating.
• Official Details: View Winona Farmers Market Updates

Mentone Egg Festival (Late May)

• The Vibe: A historic three-day festival located in neighboring Mentone (the "Egg Basket of the Midwest") celebrating its poultry-raising heritage.
• The Highlights: Features a downtown parade, flea markets, craft booths, a car/tractor show, a 5K run, and a wide variety of family-friendly games (including an egg toss and a backyard BBQ cookoff).
• Official Details: View Mentone Egg Festival Details

Fat & Skinny Tire Fest (May)

• The Vibe: A massive, weekend-long celebration of all things cycling that draws thousands of racers, casual riders, and spectators from all over the Midwest.
• The Highlights: Exciting road and mountain bike races, scenic countryside tours, family activities, kids' events, food trucks, and live music.
• The Wanderer’s Rest Advantage: Skip the parking hassle! Ride your bike right from our doorstep straight to the festival hub. We offer plenty of space to store gear and unwind after a long day in the saddle.
• Official Schedule & Details: View Fat & Skinny Tire Fest Details

The Village Art Fair (June)

• The Vibe: One of Northern Indiana's most scenic and popular fine art shows, beautifully hosted along the canal.
• The Highlights: Browse and purchase original works from nearly 70 juried artists traveling from across the country, alongside live music, kids' activities, and local food vendors.
• Official Schedule & Details: View Village Art Fair Details

Warsaw Optimist Triathlon (Late June)

• The Vibe: An iconic, high-energy community tradition celebrating over three decades of athletic excellence at Winona Lake Park.
• The Highlights: Competitors push their limits through a scenic lake swim, a fast-paced regional bike segment, and an energetic run routing directly along our beautiful local Greenway trails. Whether you are aiming for a personal record or cheering from the sidelines, the atmosphere in the Village is electric.
• The Wanderer’s Rest Advantage: The ultimate home base for athletes! Skip the morning transit log-jam—we are just minutes from the starting line and offer secure, dry bicycle storage to keep your high-end gear safe.
• Official Details: View Triathlon Details

Independence Day Fireworks Festival (Early July)

• The Vibe: Classic, small-town Americana at its absolute best, with the community gathering around the water and the Village.
• The Highlights: An outdoor concert by the Symphony of the Lakes at the Miller Sunset Pavilion followed by a spectacular, coordinated fireworks display over Winona Lake at dusk.
• The Wanderer’s Rest Advantage: The Village experiences traffic gridlock and parking shortages on the 4th of July. As our guest, you can leave your cars parked safely in our private drive and stroll down to the beach or pavilion in less than 5 minutes. When the show ends, walk right past the traffic jam straight back to our private yard and fire pit!
• Official Schedule & Details: View Fireworks Festival Details

Dixie Day Festival & Art Fair (Late July)

• The Vibe: A premier, highly popular lake heritage festival hosted in nearby North Webster.
• The Highlights: Take a 75-minute narrated cruise on the historic Dixie Sternwheeler (Indiana's oldest operating paddleboat, built in 1929). The festival also features an arts and crafts fair, an open-air market, a car/boat show, a 5K run, and a food court.
• Official Details: View Dixie Day Festival Details

Village Jazz Festival (July)

• The Vibe: A relaxing day of free, live, outdoor jazz entertainment in a gorgeous lakeside setting.
• The Highlights: Incredible performances ranging from big bands to intimate small ensembles, hosted at local venues like the Rodeheaver Auditorium or the Miller Sunset Pavilion. Local food trucks are on-site to serve up amazing food and refreshments!
• Official Schedule & Details: View Village Jazz Festival Details

Touch-a-Truck (Late July)

• The Vibe: A wildly popular, interactive community event where children (and kids at heart) can get up close and personal with the big machinery that keeps our town moving.
• The Highlights: Kids can climb inside, honk horns, and explore police cars, fire engines, giant dump trucks, tractors, and construction machinery parked at the Miller Sunset Pavilion. Perfect for families booking a mid-summer lake trip!
• Official Details: View Touch-a-Truck Details

Village Sidewalk Sale (August)

• The Vibe: A massive, end-of-summer shopping extravaganza throughout the Village.
• The Highlights: Stroll the tree-lined streets and shop clearance tables directly on the sidewalks. Participating boutiques, gear shops, and markets offer incredible clearance deals.
• Official Details: View Sidewalk Sale Details

Canal Days & Cardboard Boat Regatta (August)

• The Vibe: A high-energy, incredibly fun end-of-summer celebration along the canal.
• The Highlights: Stroll craft and art booths, enjoy delicious canal-side food vendors, and participate in family-friendly activities. The day wraps up with the hilarious and competitive annual Cardboard Boat Regatta!
• Official Schedule & Details: View Canal Days Details

Pierceton Heirloom Tomato Festival (Late August)

• The Vibe: A unique agricultural celebration hosted in neighboring Pierceton, famous for attracting garden enthusiasts and families alike.
• The Highlights: Features an exhibition of over 100 rare heirloom tomato varieties with complimentary public tastings, a 5K run/walk, live music, craft vendors, and a judged agricultural art show at Brower Park.
• Official Details: View Heirloom Tomato Festival Details

Winona Lake Sunset Pickleball Tournament (Mid-September)

• The Vibe: A premier, highly popular regional sports weekend that draws hundreds of players and families to the lake.
• The Highlights: Spanning a full three-day weekend on the beautiful outdoor courts at Winona Lake Park, this tournament features competitive brackets for all ages and skill levels, vibrant local food trucks, and great community energy. Every registration directly supports local and global disaster relief efforts through the World Compassion Network.
• Official Registration & Brackets: View Sunset Pickleball Tournament Details

Winona Lake Trail Fest (Late September)

• The Vibe: A high-energy, community-focused weekend celebrating outdoor recreation, trail running, and mountain biking on our world-class trail system.
• The Highlights: Features trail run/walk races (5k and 10k), endurance mountain bike relay races (6 and 12-hour), kids' MTB clinics, a kids' night ride, live music, and food trucks—with all proceeds supporting local trail maintenance and park expansions.
• The Wanderer’s Rest Advantage: Located just a 5-minute walk from the Winona Lake Trailhead, our property serves as the ultimate staging ground for racing teams and outdoor groups. Enjoy secure space for gear, plenty of room to clean up after the muddy trails, and a private fire pit to swap trail stories at night.
• Official Schedule & Details: View Winona Lake Trail Fest Details

Christmas Shopping Extravaganza (Early November)

• The Vibe: Get a jump start on your holiday shopping with a festive, cheerful atmosphere.
• The Highlights: Special storewide discounts, custom holiday gift guides, live giveaways, and hot cocoa in every boutique.
• Official Details: View Holiday Extravaganza Details

The Village Tree Lighting Ceremony (Late November)

• The Vibe: A magical holiday experience for the whole family.
• The Highlights: Train rides through the brick paver streets, local Christmas carolers, cookies, hot chocolate, a visit from Santa Claus, and the official lighting of the Village Christmas Tree.
• Official Schedule & Details: View Tree Lighting Details